This paper clarifies the full extent of the differences between Jacques Maritain and Dorothy Day on pacifism and anarchism in the light of their solidarity. I argue that their differences were primarily due to the particular challenges they faced in their specific vocation arising from the World War II context, and secondarily due to their different understandings of the relationship between nature and grace. While Day became drawn to a concrete heroic life of the supernatural virtues under the guidance of her spiritual director John Hugo, Maritain aimed to philosophically elucidate all the possible means available to modern Christians which may contribute to a historical realization of the Christian ideal. Their theological difference on nature and grace did not constitute a fundamental rift if taking into account the role of conscience as the essential element of a person's dignity, where the spiritual life takes shape and discernments are made. The pure means of the philosopher and the supernatural means of the saint are united in the Christian who is willing to give all for the object of their love.